CA2964409A1 - Procedes de separation de composes aromatiques d'huiles de base lubrifiantes - Google Patents
Procedes de separation de composes aromatiques d'huiles de base lubrifiantes Download PDFInfo
- Publication number
- CA2964409A1 CA2964409A1 CA2964409A CA2964409A CA2964409A1 CA 2964409 A1 CA2964409 A1 CA 2964409A1 CA 2964409 A CA2964409 A CA 2964409A CA 2964409 A CA2964409 A CA 2964409A CA 2964409 A1 CA2964409 A1 CA 2964409A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl group
- formula
- silicon atom
- nitrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 131
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 178
- 229910052710 silicon Inorganic materials 0.000 claims description 213
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 212
- 239000000178 monomer Substances 0.000 claims description 202
- 125000000217 alkyl group Chemical group 0.000 claims description 196
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 143
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 116
- 125000003545 alkoxy group Chemical group 0.000 claims description 115
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 115
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 100
- 125000002947 alkylene group Chemical group 0.000 claims description 89
- -1 methoxy, ethoxy Chemical group 0.000 claims description 85
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 62
- 239000003463 adsorbent Substances 0.000 claims description 55
- 239000011148 porous material Substances 0.000 claims description 50
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000004450 alkenylene group Chemical group 0.000 claims description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
- 229910052782 aluminium Inorganic materials 0.000 claims description 31
- 125000004122 cyclic group Chemical group 0.000 claims description 31
- 238000001179 sorption measurement Methods 0.000 claims description 30
- 125000004419 alkynylene group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- 229920002396 Polyurea Polymers 0.000 claims description 27
- 238000000926 separation method Methods 0.000 claims description 26
- 229910052796 boron Inorganic materials 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000010457 zeolite Substances 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 239000013335 mesoporous material Substances 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- 229910044991 metal oxide Inorganic materials 0.000 claims description 12
- 150000004706 metal oxides Chemical class 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 10
- 229910021482 group 13 metal Inorganic materials 0.000 claims description 9
- 230000000737 periodic effect Effects 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 239000012229 microporous material Substances 0.000 claims description 4
- 229910003849 O-Si Inorganic materials 0.000 claims description 2
- 229910003872 O—Si Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 140
- 239000002585 base Substances 0.000 description 54
- 229910052751 metal Inorganic materials 0.000 description 46
- 239000002184 metal Substances 0.000 description 46
- 239000010936 titanium Substances 0.000 description 46
- 229910052719 titanium Inorganic materials 0.000 description 46
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 45
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 43
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 43
- 229910052726 zirconium Inorganic materials 0.000 description 43
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 38
- 239000000203 mixture Substances 0.000 description 38
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- 125000004475 heteroaralkyl group Chemical group 0.000 description 32
- 239000011230 binding agent Substances 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 23
- 239000007983 Tris buffer Substances 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- 150000002430 hydrocarbons Chemical class 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 21
- SPEDTQCGQOZHQP-UHFFFAOYSA-N 1,1,3,3,5,5-hexaethoxy-1,3,5-trisilinane Chemical compound CCO[Si]1(OCC)C[Si](OCC)(OCC)C[Si](OCC)(OCC)C1 SPEDTQCGQOZHQP-UHFFFAOYSA-N 0.000 description 21
- 229930195733 hydrocarbon Natural products 0.000 description 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 20
- 239000004215 Carbon black (E152) Substances 0.000 description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 16
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 16
- 239000003361 porogen Substances 0.000 description 16
- 229910021536 Zeolite Inorganic materials 0.000 description 15
- LFMQNMXVVXHZCC-UHFFFAOYSA-N 1,3-benzothiazol-2-yl n,n-diethylcarbamodithioate Chemical compound C1=CC=C2SC(SC(=S)N(CC)CC)=NC2=C1 LFMQNMXVVXHZCC-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001923 cyclic compounds Chemical class 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- 241000894007 species Species 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 10
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000013522 chelant Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000006548 C4-10 heterocycloalkyl group Chemical group 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 8
- QWOVEJBDMKHZQK-UHFFFAOYSA-N 1,3,5-tris(3-trimethoxysilylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)N(CCC[Si](OC)(OC)OC)C(=O)N(CCC[Si](OC)(OC)OC)C1=O QWOVEJBDMKHZQK-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 238000001354 calcination Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 230000008929 regeneration Effects 0.000 description 7
- 238000011069 regeneration method Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 229920001983 poloxamer Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000005595 acetylacetonate group Chemical group 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 235000010215 titanium dioxide Nutrition 0.000 description 4
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 3
- MQEFJQBNYDQNSM-UHFFFAOYSA-N 1,3,5-triethoxy-1,3,5-trimethyl-1,3,5-trisilinane Chemical compound CCO[Si]1(C)C[Si](C)(OCC)C[Si](C)(OCC)C1 MQEFJQBNYDQNSM-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000000413 hydrolysate Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 125000006301 indolyl methyl group Chemical group 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012621 metal-organic framework Substances 0.000 description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 3
- 238000000696 nitrogen adsorption--desorption isotherm Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 230000008520 organization Effects 0.000 description 3
- 239000003348 petrochemical agent Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 3
- NIINUVYELHEORX-UHFFFAOYSA-N triethoxy(triethoxysilylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)C[Si](OCC)(OCC)OCC NIINUVYELHEORX-UHFFFAOYSA-N 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- RTLBCONNYYAZQQ-UHFFFAOYSA-N (2,2,4,4,6,6-hexaethoxy-3,5-disilylcyclohexyl)silane Chemical compound C(C)OC1(C(C(C(C(C1[SiH3])(OCC)OCC)[SiH3])(OCC)OCC)[SiH3])OCC RTLBCONNYYAZQQ-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- MFLKDEMTKSVIBK-UHFFFAOYSA-N zinc;2-methylimidazol-3-ide Chemical compound [Zn+2].CC1=NC=C[N-]1.CC1=NC=C[N-]1 MFLKDEMTKSVIBK-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
- B01D53/0462—Temperature swing adsorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
- B01D53/047—Pressure swing adsorption
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/0203—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising compounds of metals not provided for in B01J20/04
- B01J20/0225—Compounds of Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt
- B01J20/0229—Compounds of Fe
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
L'invention concerne des procédés de séparation d'un composé aromatique d'une huile de base lubrifiante. Le procédé consiste à mettre une huile de base lubrifiante contenant un composé aromatique en contact avec un matériau d'organosilice tel que fourni ici.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US201462091077P | 2014-12-12 | 2014-12-12 | |
US201462091071P | 2014-12-12 | 2014-12-12 | |
US62/091,071 | 2014-12-12 | ||
US62/091,077 | 2014-12-12 | ||
PCT/US2015/065306 WO2016094830A1 (fr) | 2014-12-12 | 2015-12-11 | Procédés de séparation de composés aromatiques d'huiles de base lubrifiantes |
Publications (1)
Publication Number | Publication Date |
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CA2964409A1 true CA2964409A1 (fr) | 2016-06-16 |
Family
ID=56566576
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2964409A Abandoned CA2964409A1 (fr) | 2014-12-12 | 2015-12-11 | Procedes de separation de composes aromatiques d'huiles de base lubrifiantes |
CA2964969A Active CA2964969C (fr) | 2014-12-12 | 2015-12-11 | Procedes de fabrication de membrane a l'aide de materiaux a base d'organosilice et leurs utilisations |
CA2967047A Abandoned CA2967047A1 (fr) | 2014-12-12 | 2015-12-11 | Materiaux organosilicies et leurs utilisations |
CA2964385A Expired - Fee Related CA2964385C (fr) | 2014-12-12 | 2015-12-11 | Catalyseurs d'hydrogenation d'arenes et utilisations associees |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2964969A Active CA2964969C (fr) | 2014-12-12 | 2015-12-11 | Procedes de fabrication de membrane a l'aide de materiaux a base d'organosilice et leurs utilisations |
CA2967047A Abandoned CA2967047A1 (fr) | 2014-12-12 | 2015-12-11 | Materiaux organosilicies et leurs utilisations |
CA2964385A Expired - Fee Related CA2964385C (fr) | 2014-12-12 | 2015-12-11 | Catalyseurs d'hydrogenation d'arenes et utilisations associees |
Country Status (8)
Country | Link |
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US (3) | US10266622B2 (fr) |
EP (4) | EP3229944A1 (fr) |
JP (1) | JP6755872B2 (fr) |
CN (1) | CN107001945B (fr) |
CA (4) | CA2964409A1 (fr) |
DK (1) | DK3230410T3 (fr) |
SG (4) | SG11201702541XA (fr) |
ZA (1) | ZA201805434B (fr) |
Families Citing this family (20)
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CA2964965A1 (fr) * | 2014-12-12 | 2016-06-16 | Exxonmobil Research And Engineering Company | Procedes de revetement utilisant des materiaux d'organosilice, et utilisations correspondantes |
WO2016094848A1 (fr) | 2014-12-12 | 2016-06-16 | Exxonmobil Chemical Patents Inc. | Matériaux organosiliciés destiné à être utilisés en tant qu'adsorbants pour l'élimination de composés oxygénés |
US10183272B2 (en) | 2014-12-12 | 2019-01-22 | Exxonmobil Research And Engineering Company | Adsorbent for heteroatom species removal and uses thereof |
WO2016094769A1 (fr) | 2014-12-12 | 2016-06-16 | Exxonmobil Research And Engineering Company | Catalyseurs d'hydrogénation d'arènes et utilisations associées |
EP3229952B1 (fr) * | 2014-12-12 | 2019-01-23 | ExxonMobil Research and Engineering Company | Matériaux organosiliciés |
US10576453B2 (en) | 2014-12-12 | 2020-03-03 | Exxonmobil Research And Engineering Company | Membrane fabrication methods using organosilica materials and uses thereof |
US10207249B2 (en) | 2014-12-12 | 2019-02-19 | Exxonmobil Research And Engineering Company | Organosilica materials and uses thereof |
US10155826B2 (en) | 2014-12-12 | 2018-12-18 | Exxonmobil Research And Engineering Company | Olefin polymerization catalyst system comprising mesoporous organosilica support |
EP3229944A1 (fr) * | 2014-12-12 | 2017-10-18 | ExxonMobil Research and Engineering Company | Procédés de fabrication de membrane à l'aide de matériaux à base d'organosilice et leurs utilisations |
WO2016094843A2 (fr) * | 2014-12-12 | 2016-06-16 | Exxonmobil Chemical Patents Inc. | Système de catalyseur de polymérisation d'oléfine comprenant un support à base d'organosilice mésoporeuse |
EP3034476A1 (fr) * | 2014-12-16 | 2016-06-22 | Heraeus Quarzglas GmbH & Co. KG | Procédé de fabrication de verre de quartz synthétique à l'aide d'un dispositif de purification |
US10414887B2 (en) | 2015-10-02 | 2019-09-17 | Exxonmobil Chemical Patents Inc. | Supported catalyst systems and methods of using same |
US10435514B2 (en) | 2016-06-10 | 2019-10-08 | Exxonmobil Research And Engineering Company | Organosilica materials, methods of making, and uses thereof |
WO2017213669A1 (fr) * | 2016-06-10 | 2017-12-14 | Exxonmobil Research And Enginering Company | Procédés de production de matériaux à base d'organosilice et leurs utilisations |
WO2017213668A1 (fr) | 2016-06-10 | 2017-12-14 | Exxonmobil Research And Engineering Company | Catalyseurs à base de polymères d'organosilice et leurs procédés de production |
US10179839B2 (en) | 2016-11-18 | 2019-01-15 | Exxonmobil Research And Engineering Company | Sulfur terminated organosilica materials and uses thereof |
US11111352B2 (en) | 2017-12-21 | 2021-09-07 | Exxonmobil Research And Engineering Company | Methods of producing organosilica materials and uses thereof |
CN108715436B (zh) * | 2018-05-29 | 2019-11-08 | 四川天采科技有限责任公司 | 半导体制程常压废氢气全温程变压吸附提纯再利用的方法 |
US11370973B2 (en) * | 2020-07-10 | 2022-06-28 | Saudi Arabian Oil Company | Processes and systems for producing one or more of benzene, toluene, or mixed xylenes |
CN114804324B (zh) * | 2022-05-17 | 2023-03-10 | 山东新华制药股份有限公司 | 一种多巴类生产废水的氧化处理方法 |
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-
2015
- 2015-12-11 EP EP15820943.7A patent/EP3229944A1/fr not_active Withdrawn
- 2015-12-11 US US15/526,529 patent/US10266622B2/en not_active Expired - Fee Related
- 2015-12-11 US US15/526,512 patent/US10239967B2/en not_active Expired - Fee Related
- 2015-12-11 SG SG11201702541XA patent/SG11201702541XA/en unknown
- 2015-12-11 EP EP15826222.0A patent/EP3230410B1/fr not_active Not-in-force
- 2015-12-11 CA CA2964409A patent/CA2964409A1/fr not_active Abandoned
- 2015-12-11 EP EP15825983.8A patent/EP3230325B1/fr active Active
- 2015-12-11 JP JP2017531182A patent/JP6755872B2/ja not_active Expired - Fee Related
- 2015-12-11 EP EP15828704.5A patent/EP3230409A1/fr not_active Withdrawn
- 2015-12-11 SG SG11201702538PA patent/SG11201702538PA/en unknown
- 2015-12-11 SG SG11201702452UA patent/SG11201702452UA/en unknown
- 2015-12-11 CA CA2964969A patent/CA2964969C/fr active Active
- 2015-12-11 US US14/966,015 patent/US10544239B2/en active Active
- 2015-12-11 DK DK15826222.0T patent/DK3230410T3/da active
- 2015-12-11 CA CA2967047A patent/CA2967047A1/fr not_active Abandoned
- 2015-12-11 SG SG11201702603RA patent/SG11201702603RA/en unknown
- 2015-12-11 CA CA2964385A patent/CA2964385C/fr not_active Expired - Fee Related
- 2015-12-11 CN CN201580067126.3A patent/CN107001945B/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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ZA201805434B (en) | 2019-06-26 |
CA2964969C (fr) | 2022-11-15 |
JP2018501227A (ja) | 2018-01-18 |
CA2964385A1 (fr) | 2016-06-16 |
CA2964385C (fr) | 2021-06-01 |
EP3229944A1 (fr) | 2017-10-18 |
CN107001945B (zh) | 2020-12-18 |
SG11201702452UA (en) | 2017-06-29 |
US10266622B2 (en) | 2019-04-23 |
US20170320977A1 (en) | 2017-11-09 |
CA2967047A1 (fr) | 2016-06-16 |
EP3230325A1 (fr) | 2017-10-18 |
US10239967B2 (en) | 2019-03-26 |
JP6755872B2 (ja) | 2020-09-16 |
EP3230410B1 (fr) | 2019-04-10 |
EP3230410A1 (fr) | 2017-10-18 |
SG11201702603RA (en) | 2017-06-29 |
CN107001945A (zh) | 2017-08-01 |
DK3230410T3 (da) | 2019-07-01 |
SG11201702538PA (en) | 2017-06-29 |
EP3230325B1 (fr) | 2020-06-17 |
SG11201702541XA (en) | 2017-06-29 |
EP3230409A1 (fr) | 2017-10-18 |
US10544239B2 (en) | 2020-01-28 |
US20170320971A1 (en) | 2017-11-09 |
US20160229959A1 (en) | 2016-08-11 |
CA2964969A1 (fr) | 2016-06-16 |
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